730992-70-8

Upstream product

• 344-04-7 bromopentafluorobenzene 
• 653-37-2 perfluorobenzaldehyde 

Downstream Products

• 1029433-33-7 (1S,2S)-1,2-bis(2,3,5,6-tetrafluorophenyl)ethane-1,2-diamine 
• 1029433-22-4 (1S,2S)-1,2-bis(4-methoxy-2,3,5,6-tetrafluorophenyl)ethane-1,2-diamine 
• 1029433-25-7 (1S,2S)-1,2-bis(4-benzhydryloxy-2,3,5,6-tetrafluorophenyl)ethane-1,2-diamine 
• 1029433-24-6 (1S,2S)-1,2-bis(4-(pentan-3-yloxy)-2,3,5,6-tetrafluorophenyl)ethane-1,2-diamine 
• 1029433-26-8 (1S,2S)-1,2-bis(4-neopentyloxy-2,3,5,6-tetrafluorophenyl)ethane-1,2-diamine 
• 1029433-27-9 (1S,2S)-1,2-bis(4-cyclopentyloxy-2,3,5,6-tetrafluorophenyl)ethane-1,2-diamine 
• 1029433-29-1 (1S,2S)-1,2-bis(2,3,5,6-tetrafluoro-4-(3,3,5,5-tetramethylcyclohexyloxy)phenyl)ethane-1,2-diamine 
• 1029433-31-5 (1S,2S)-1,2-bis(4-((S)-1-phenylethoxy)-2,3,5,6-tetrafluorophenyl)ethane-1,2-diamine 
• 1029433-32-6 (1S,2S)-1,2-bis(4-((R)-1-phenylethoxy)-2,3,5,6-tetrafluorophenyl)ethane-1,2-diamine 
• 1029433-23-5 (1S,2S)-1,2-bis(4-isopropoxy-2,3,5,6-tetrafluorophenyl)ethane-1,2-diamine 
• 1029433-28-0 (1S,2S)-1,2-bis(4-cyclohexyloxy-2,3,5,6-tetrafluorophenyl)ethane-1,2-diamine 

Relevant academic research and scientific papers

Mechanistic studies inform design of improved Ti(salen) catalysts for enantioselective [3 + 2] cycloaddition

Ti(salen) complexes catalyze the asymmetric [3 + 2] cycloaddition of cyclopropyl ketones with alkenes. While high enantioselectivities are achieved with electron-rich alkenes, electron-deficient alkenes are less selective. Herein, we describe mechanistic studies to understand the origins of catalyst and substrate trends in an effort to identify a more general catalyst. Density functional theory (DFT) calculations of the selectivity determining transition state revealed the origin of stereochemical control to be catalyst distortion, which is largely influenced by the chiral backbone and adamantyl groups on the salicylaldehyde moieties. While substitution of the adamantyl groups was detrimental to the enantioselectivity, mechanistic information guided the development of a set of eight new Ti(salen) catalysts with modified diamine backbones. These catalysts were evaluated with four electron-deficient alkenes to develop a three-parameter statistical model relating enantioselectivity to physical organic parameters. This statistical model is capable of quantitative prediction of enantioselectivity with structurally diverse alkenes. These mechanistic insights assisted the discovery of a new Ti(salen) catalyst, which substantially expanded the reaction scope and significantly improved the enantioselectivity of synthetically interesting building blocks.

A New, Short, and Stereocontrolled Synthesis of C2-Symmetric 1,2-Diamines

The previously unknown 5-spirocyclohexylisoimidazole has been made efficiently and simply by reaction of ammonia, glyoxal hydrate, and cyclohexanone. It is a very useful precursor for the diastereocontrolled synthesis of many C2-symmetric 1,2-diamines, a class which is important for the generation of a variety of C2-symmetric reagents and catalysts for enantioselective synthesis.

Synthesis of enantiomerically pure (R,R)- and (S,S)-1,2-Bis(pentafluorophenyl)ethane-1,2-diamine and evaluation of the pK a value by ab initio calculations

1,2-Bis(pentafluorophenyl)ethane-1,2-diamine (1) was synthesized by the imino pinacol coupling of 4-methoxy-N-(pentafluorobenzylidene)benzylamine using a Zn-Cu couple and p-TsOH·H2O. The optical resolution of (±)-1 by means of chiral HPLC gave